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You will need to use "Search Indenting" to group the processing of the 'and/or' evaluations. Indent a row by right clicking on the row and move right.
Try
" Actionable Date <= today"
"or - Actionable Date - Equals - ______"
<indent> and "Icon - equals - <task>"
<indent> and "Category - equal - <Junk>"
For me, understanding the logic of the Criteria Grid, took more than a brief read of the help file.
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